Sulfamic Acid → 6-(2,6-dichlorophenyl)-2-N-[4-(diethylamino)butyl]pyrido[2,3-d]pyrimidine-2,7-diamine

HRID 617949

Reaktionsgleichung

Reaktionsgleichung von HRID 617949
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9]([NH2:20])=[N:8][C:6]=2[N:7]=1.S(=O)(=O)(O)N.[CH2:26]([N:28]([CH2:31][CH2:32][CH2:33][CH2:34]N)[CH2:29][CH3:30])[CH3:27]>>[Cl:19][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([Cl:18])[C:12]=1[C:10]1[C:9]([NH2:20])=[N:8][C:6]2[N:7]=[C:2]([NH:1][CH2:34][CH2:33][CH2:32][CH2:31][N:28]([CH2:29][CH3:30])[CH2:26][CH3:27])[N:3]=[CH:4][C:5]=2[CH:11]=1

Komponenten

4

Edukt 3

HCID 5987Sulfamic AcidHCID 117976N,N-Diethyl-1,4-butanediamineHCID 53281136-(2,6-Dichlorophenyl)pyrido[2,3-d]pyrimidine-2,7-diamine

Produkt 1

HCID 53281336-(2,6-dichlorophenyl)-2-N-[4-(diethylamino)butyl]pyrido[2,3-d]pyrimidine-2,7-diamine

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (40 g) from Example 1, sulfamic acid (25.4 g) and diethylaminobutylamine (205 mL) was heated to approximately 150° C. for 28 hours. The reaction temperature was lowered to 50° C., and excess diethylaminobutylamine was removed in vacuo. After cooling to 25° C., the residue was suspended in water. The aqueous solution was made alkaline with a solution of saturated sodium bicarbonate and extracted with dichloromethane several times. The dichloromethane layers were combined, washed several times, first with a saturated solution of sodium bicarbonate then a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was washed repeatedly with diethyl ether and then crystallized from ethyl acetate. The recrystallized product was further purified by column chromatography, eluting first with ethyl acetate:methyl alcohol:triethylamine (85:14:1) followed by ethyl acetate:ethyl alcohol:triethylamine (9:2:1) to afford 36.2 g of the title compound 6-(2,6-dichlorophenyl)-N2 -(4-diethylamino-butyl)-pyrido[2,3-d]pyrimidine-2,7-diamine, CIMS (1% N3 in CH4): 461=M+ +C2H5, 433=M+ +H (Base), 417, 403, 360.

Aufarbeitung

  1. customwas lowered to 50° C.
  2. customexcess diethylaminobutylamine was removed in vacuo
  3. temperatureAfter cooling to 25° C.
  4. extractionextracted with dichloromethane several times
  5. washwashed several times
  6. dry with materialfirst with a saturated solution of sodium bicarbonate then a saturated solution of sodium chloride, dried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. washThe residue was washed repeatedly with diethyl ether
  9. customcrystallized from ethyl acetate
  10. customThe recrystallized product was further purified by column chromatography
  11. washeluting first with ethyl acetate:methyl alcohol:triethylamine (85:14:1)

Quellen und Nachweise

ORD-Eintrag
ord-3bdc5d55884c47c4ac67a97f78fd03f9
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05952342

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